3six5dates

Four women in four cities take on 365 dates between them. Follow their adventures and misadventures.

25. That Was Fast! Mr. VIP

Sitting at our private, bottle-service only table at Ajna Bar, Mr. VIP (Very Important Person), reminded me of our recent Facebook chat.

When I mentioned all the men I was dating through 3six5dates, he wrote:
“Good, they are keeping you on ice – for me.”

So it seems!

It was the end of what can only be described as an AMAZING night, and I laughed, remembering his persistence.

He had been asking me out for months since the moment I “took his breath away” when he spotted me at Starbucks.

And if it wasn’t for this social experiment, we would not be here. He is 43 years old, need I say more?

However, there was a certain breed of romantic chemistry that defied age and – clearly – we had it.

The hostess at the upscale STK sat us in the front of the restaurant, and said:

“We put the beautiful people here – you two make us look good.”

Indeed! Hard not to look good while next to a hot guy – in a white suit!

Mr. VIP was real smooth. He did not blink an eye when I ordered a $45 piece of fish, but instead ordered some incredible sides to go with it.

Parmesan Truffle fries = Heaven.

Mid-meal, he kissed me on the way to the bathroom, as if we had been dating forever. 

Sooo setting the stage for later.

He intrigued me with inspiring stories of his accomplishments and family background; when I say something funny, he really laughs.

Afterward, I intrigued him by confidently and passionately talking business with his friends and business partners.

“You’ve always impressed me. You’re such the business woman, but you’re so girly!  You complement me. What are you doing for Labor Day?”

Then, Mr. VIP gave me the invite of all invites:

Four days, all-expenses paid at an Estate in the exclusive Hamptons with him and his business partners.

He painted a picture of us lounging poolside by day, working the room at night.

We would be the talk of the exclusive parties he’d be hosting for NY’s elite professionals in media and fashion.

He sees me as half of a power couple – and he wants in.

“It would be a fun way for us to get to know each other, and it could be a great way for you to promote your new projects and get new clients – all eyes on us.”

Ummm, hello, how can I say no? 

“Well, it sounds perfect and I totally want to, but it’s so soon and I don’t want there to be any ‘expectations’ for us.”

Mr. VIP reassured me he was not just trying to sleep with me…but apparently other people did! 

Well, okay, at least one person…

Enter Exhibit A: Leaving the bar, we stopped and talked to a middle-aged Ecuadorian woman who was smiling at us from ear to ear.  Upon mentioning her husband, she looked straight at us and said, “We share.”

By the look of her raised eyebrow and sly grin, we knew she meant more than just closet space!

We walked away laughing, glowing, and chatting about how this has never happened to either of us.

At home, I wondered what other firsts I would have on my first Hamptons trip!

Going away with a 43-year-old guy after just one date feels so wrong – yet so right.

What do you think? Is it a good idea to go away with someone after just one date?

Have you ever agreed to this? How did it turn out?

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  • Anonymous

    I enjoy reading these articles. It’s really interesting to hear these
    stories. I don’t agree with your approach. You knew the guy wanted to
    have sex with you in the end. You knew you weren’t going to have sex
    with him….So why not say you’re just interested as being
    friends?….answer: cos you knew you wouldn’t have gotten the 4-day all
    expenses paid trip……Manipulation is the main problem facing the
    dating world for guys. When guys can be honest in stating what they
    want, girls would be honest in stating what they want.

    • Giovannia Ja

      Agree with the guy above^

  • Bella

    *career

  • Rachel Russo – Ms. New York

    The beauty of this is that no one has to agree with my approach! (But
    totally has the right to express this!) I wanted to be more than friends
    with this guy. If you keep reading, you’ll see that. Re: Sex–Let’s
    face it, most guys want to have sex with the women they date in the end.
    Does that mean women shouldn’t go out with them because they don’t know
    they instantly want to have sex after a first date? I think not!

  • POPE JOHNSON

    It was the end of what can only be described as an AMAZING night, and I
    laughed, remembering his persistence.

    He had been asking me out for months since the moment I took his
    breath away when he spotted me at Starbucks.

    And if it wasn’t for this social experiment, we would not be here. He
    is 43 years old, need I say more

    SO YOUVE BEEN DENYING HIM FOR MONTHS BUT YOU CLEARLY DONT WANT HIM,
    UNTIL THIS EXPERIMENT, AND NOW THAT HES SPENDING TONS OF MONEY ON YOU
    YOU FINALLY AGREE TO GO WITH HIM… SO HOW MUCH MONEY DOES HE HAVE TO
    SPEND BEFORE YOU GIVE HIM WHAT HE REALLY WANTS? THE SEX… I DONT THINK
    YOURE FOOLING ANYBODY HERE… UNLESS YOURE ACTUALLY A PROSTITUTE.. THEN
    I GUESS IT ALL MAKES SENSE

  • POPE JOHNSON

    OWNED…

  • Tali

    Rachel, of course I already read many more of your posts, but I just
    wanted to give you my support after this guy’s trolling post. I
    understand how hard it is to decide to break your rules on dates, and
    date older guys, and deal with the guys expectations that you have to
    “do it” on the first few dates. You’re perfectly free to not have wanted
    to date him, then date him, then like him and still wait to have sex,
    then give up, if you feel like it, without feeling any obligation of
    sleeping with him because he spent so much on you. Just be as truthful
    to yourself as possible and we’ll be on your side! (the good ones among
    us anyway ;)

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